Method of making glycerol monoesters

Abstract

Described is a method of producing compositions comprising a high concentration of glycerol monoesters. The method entails reacting a mixture of glycerol, a fatty acid source, and water, in the absence of catalysts, at a temperature preferably from about 180° C. to about 300° C., a pressure preferably from about 15 psig to 400 psig, and for a time sufficient to yield an acid value of preferably from about 2.0 to about 7.0 in the mixture, and a hydroxyl value preferably of from about 260 to about 460 in the mixture. The method can be used to make lipid mixtures comprising 90 wt % or more of glycerol monoesters. The method does not require molecular distillation.

1 . A method of producing a composition of matter comprising glycerol monoesters, the method comprising: reacting a mixture comprising glycerol, a fatty acid source, and water, and devoid of catalysts, at an elevated temperature and at an elevated pressure wherein the glycerol and the water have increased solubility in the fatty acid source as compared to their respective solubilities at room temperature and atmospheric pressure, for a time sufficient to generate a composition of matter comprising at least about 50 wt % glycerol monoesters. 
   
   
       2 . The method of  claim 1 , comprising reacting the mixture at a temperature of from about 180° C. to about 300° C. 
   
   
       3 . The method of  claim 1 , comprising reacting the mixture at a temperature of from about 200° C. to about 260° C. 
   
   
       4 . The method of any one of  claims 1 ,  2 , or  3 , comprising reacting the mixture at a pressure of from about 15 psig to about 400 psig. 
   
   
       5 . The method of  claim 4 , comprising reacting the mixture for a time sufficient to yield an acid value of from about 2.0 to about 7.0 in the mixture. 
   
   
       6 . The method of  claim 5 , comprising reacting the mixture for a time sufficient to yield a hydroxyl value of from about 260 to about 460 in the mixture. 
   
   
       7 . The method of  claim 6 , comprising reacting the mixture for a time sufficient to yield a composition of matter comprising at least about 90 wt % glycerol mono esters. 
   
   
       8 . The method of any one of  claims 1 ,  2 , or  3 , comprising reacting the mixture at a pressure of from about 30 psig to about 75 psig. 
   
   
       9 . The method of  claim 8 , comprising reacting the mixture for a time sufficient to yield an acid value of from about 2.0 to about 7.0 in the mixture. 
   
   
       10 . The method of  claim 9 , comprising reacting the mixture for a time sufficient to yield a hydroxyl value of from about 260 to about 460 in the mixture. 
   
   
       11 . The method of  claim 10 , comprising reacting the mixture for a time sufficient to yield a composition of matter comprising at least about 90 wt % glycerol monoesters. 
   
   
       12 . The method of  claim 1 , further comprising, after the reacting step, removing excess glycerol from the mixture. 
   
   
       13 . The method of  claim 1 , wherein the fatty acid source comprises a fatty acid in free acid form. 
   
   
       14 . The method of  claim 1 , wherein the fatty acid source comprises a glyceride. 
   
   
       15 . The method of  claim 1 , wherein the fatty acid source comprises a purified fatty acid selected from the group consisting of decanoic acid, lauric acid, myristic acid, palmitic acid, pentadecanoic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, margaric acid, myristoleic acid, palmitoleic acid, oleic acid, gadoleic acid, erucic acid, ricinoleic acid, linoleic acid, linolenic acid, licanic acid, margaroleic acid, arachidonic acid clupanadonic acid, eicosapentaenoic acid, and docosahexaenoic acid. 
   
   
       16 . The method of  claim 1 , wherein the fatty acid source comprises a natural oil or fat. 
   
   
       17 . The method of  claim 1 , wherein the natural oil or fat is selected from the group consisting of animal fats, soya bean oil, coconut oil, palm oil, palm kernel oil, rapeseed oil, cottonseed oil, linseed oil, sunflower oil, fish oil, and algae oil. 
   
   
       18 . A method of producing a composition of matter comprising glycerol monoesters, the method comprising:
 reacting a mixture comprising glycerol, a fatty acid source, and water, and devoid of catalysts, at a temperature of from about 180° C. to about 300° C., and a pressure of from about 15 psig to 400 psig, for a time sufficient to yield an acid value of from about 2.0 to about 7.0 in the mixture, and a hydroxyl value of from about 260 to about 460 in the mixture; and then   removing excess glycerol from the mixture, thereby yielding a composition of matter comprising at least about 90 wt % glycerol monoesters.